Hydrochloric Acid → Acetamide, N-(3-bromophenyl)-2-(hydroxyimino)-

HRID 2284389Notes

Reaction equation

HRID 2284389 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[C:10](Cl)(Cl)[CH:11]([OH:13])O.Cl.[NH2:17][OH:18].S([O-])([O-])(=O)=O.[Na+].[Na+].Cl>O>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:11](=[O:13])[CH:10]=[N:17][OH:18])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 115623-BromoanilineHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 6739944Acetamide, N-(3-bromophenyl)-2-(hydroxyimino)-Yield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a 3000 mL round bottom flask, 3-bromoaniline (50 g, 0.2907 mol), water (1500 mL), chloral hydrate (57.7 g, 0.3488 mol), hydroxylamine hydrochloride (64.6 g, 0.9302 mol) and sodium sulphate (250 g) were added. To this reaction mixture was slowly added concentrated HCl (76 mL). The reaction mixture was stirred at 90° C. for 2 hours. The white precipitate was formed and was collected by filtration. The white solid was dried to provide the title compound [60 g, 85%]. 1H NMR (300 MHz, DMSO-d6): δ 12.28 (s, 1H), 10.38 (s, 1H), 8.03 (t, J=1.5 Hz, 1H), 7.62-7.65 (m, 2H), 7.29-7.31 (m, 2H). LC-MS (ESI): Calculated mass: 242.0; Observed mass [M+H]+: 243.0 (RT: 0.17 min).

Workup

  1. customThe white precipitate was formed
  2. filtrationwas collected by filtration
  3. customThe white solid was dried

Sources & evidence

ORD record
ord-0cfd40d6645c485fb4aa9b15bbd9fdcf
Source dataset
uspto-grants-2015_09
Patent number
US09145411B2

Reaction notes

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